During his professional football career, Woodruff earned a Juris Doctor (1988) from Duquesne University School of Law, which he attended full time in the evening. From 1988 to 1990 he enjoyed a dual career, simultaneously practicing law and playing football, setting precedence for the NFL and professional sports. Soon after, he became a founding partner of the law firm of Woodruff, Flaherty & Fardo, LLC.

Currently, as a judge in the Family Court he presides over cases in the Juvenile Division, considering it a privilege to be a role model and give guidance to youth, especially the young Black males who come before him. He was appointed to the prestigious Juvenile Court Judge's Commission by Governor Ed Rendell in July of 2006 to set standards for the court on a statewide basis, was appointed to Pennsylvania's Juvenile Court Rules Committee and served on the Interbranch Commission on Juvenile Justice to right the wrongs of two judges in Luzerne County. Woodruff also enjoys the opportunity he has to preside over adoptions for CYF (Children Youth & Families) each month.

In fact, Woodruff feels that his work with youth is a calling, with responsibilities that don't end with the job. Annually, he and his wife host a mentor recruitment breakfast for the Northside Urban Pathways Charter School and they also serve as the Pittsburgh co-chairs for the National Campaign to Stop Violence's "Do the Write Thing Challenge," a unique program that gives middle school students the opportunity to communicate their thoughts on the impact of youth violence on their lives and to make personal commitments to reduce violence.

Judge Woodruff's legal affiliations are with the Allegheny County and Pennsylvania Bar Associations, the Homer S. Brown Law Association and as an elected member of the Pennsylvania House of Delegates. His community affiliates include the boards of Urban League of Greater Pittsburgh, Urban Impact Foundation and Child Watch of Pittsburgh, Sigma Pi Phi (Boule) Fraternity, lifetime member of the NAACP and prior service to the American Cancer Society (Chairman of the Board), the Board of Governors at Duquesne University Law School, as chairman of the Duquesne Univ. Law Challenge for NEED (Negro Educational Emergency Drive) Program, American Red Cross board and was elected to the Allegheny County Bar Associations' Judiciary Committee which rates all candidates seeking public office.

Among his recent honors are the 2011 Legal Intelligencer Diverse Attorney Award, the 2010 Three Rivers Youth Hall of Fame Award, the 2009 Pittsburgh Courier Man of Excellence Award, the 2007 Duquesne University Law Alumni Outstanding Achievement Award, the Talk Magazine Salute for Achievement, The North Hills Monthly Magazine "Mover and Shaker of the Month" (August 2006) and the University of Louisville's "WOODRUFF ACADEMIC CENTER" which was named in his honor on November 2, 2006.




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